Reaction #531792

Reaction equation

11-bromoundecan-1-ol

p-cresol

water

potassium hydroxide

→

11-(p-tolyloxy)undecan-1-ol

Yield 100.0%

Solvents

ethanol

methylene chloride

Conditions

Workup

1. 1
   workup.WAITfollowed by 24-hour
2. 2
   Temperaturerefluxing
3. 3
   Otherthe reaction solution is moved into a separating funnel
4. 4
   Otherseparation
5. 5
   OtherAfter the organic phase was collected
6. 6
   Otherthe desiccant agent was removed by filtration
7. 7
   workup.DISTILLATIONthe solvent of the filtrate was distilled away under reduced pressure
8. 8
   workup.DISSOLUTIONThe resultant solid was re-dissolved in 50 ml of toluene
9. 9
   Washwas washed twice with 10 wt % of aqueous potassium hydroxide solution
10. 10
    Washwas then washed with 50 ml of saturated saline
11. 11
    OtherAfter that, the organic phase was collected
12. 12
    OtherThe desiccant agent was removed by filtration
13. 13
    workup.DISTILLATIONthe solvent of the filtrate was distilled away under reduced pressure

Procedure

The 11-bromoundecan-1-ol 15 (3.68 g) and 4.88 g of p-cresol were dissolved in 20 ml of ethanol, and 2.57 g of potassium hydroxide was added to that, followed by 24-hour refluxing. After cooled to room temperature, the reaction solution is moved into a separating funnel, and 100 ml of ion-exchange water and 50 ml of methylene chloride were added so as to cause separation. After the organic phase was collected and was dehydrated with sodium sulfate, the desiccant agent was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. The resultant solid was re-dissolved in 50 ml of toluene, and was washed twice with 10 wt % of aqueous potassium hydroxide solution, and was then washed with 50 ml of saturated saline. After that, the organic phase was collected, and was dehydrated with sodium sulfate. The desiccant agent was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure, to obtain 4.08 g of 11-(p-tolyloxy)undecan-1-ol 16, which is a white solid.

Source